


Dean's Diner

by johnwatsonblog



Category: Supernatural
Genre: Alternate Universe - Modern Setting, Cute, Diner Owner Dean Winchester, Diners, F/M, Fluff, Food, Homophobia, Love Confessions, M/M, Milkshakes, Nobody Dies, Pie, Prompt Fic, Sam Ships It, Slow Burn Ish, Smut, Sweet, Teacher Castiel, Transphobia, everyone ships it
Language: English
Status: In-Progress
Published: 2016-04-10
Updated: 2018-05-10
Packaged: 2018-06-01 08:30:32
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 7,691
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6510595
Author URL: https://archiveofourown.org/users/johnwatsonblog/pseuds/johnwatsonblog
Summary: <blockquote class="userstuff">
              <p>My first 'Prompt Fic.' <br/>Dean owns a proper-old school American diner with burgers, shakes and pie. Lots and lots of pie. He absolutely loves his jobs - apart from the early mornings - but something is missing from his life. Castiel is an English teacher for a local school that enjoys a cheeseburger or two. He is, currently, trying to get through the school year without ripping his hair out but being a teacher isn't as easy as people believe it is. </p><p>(Any warnings are in the notes before each chapter.)</p>
            </blockquote>





	1. Hump Day

_Bored._ For the first time this week, Dean could honestly say that he was completely and utterly bored out of his mind. It was an ordinary Wednesday afternoon and business was dragging by as slow as it always did during this time of the week. _No wonder Wednesday was referred to as the “hump day.”_ On Tuesdays and Thursdays, the diner was usually packed with loud teenagers who were let out early and Friday was always busy. Those days were easy to work as Dean wasn't standing aimlessly and he could focus all of his attention on filling orders and ensuring the college kids don't rip the red leather of the booth.  _Again._ The same college kids were currently in a booth with their cell phones glued to their foreheads and untouched notepads pushed aside to make room for their stacks of fries and thick milkshakes. It was almost scary how engrossed they seemed to be on the small screens.

In a booth a couple of spots away from the technology zombies were two police officers that were talking to each other in hushed tones over, now several, cups of coffee and just as many beignets.  _Caffeine always needs to be followed by pastry and sugar._ The pair had slowly become regulars, especially around lunch, repeatedly asking for a box of freshly made pastries or a slice each of the pie of the day.  _A genius idea on his own part._

Finally, there was a sweet elderly couple perched on two stools towards the end of the counter, reminiscing about their "courting" days over matching bowls of gumbo. They were, also, becoming regulars here to the point that Dean could guarantee seeing them at the same time on every Wednesday and Thursday now.  _He did ask once and apparently it was their "date days."_ Something about seeing their love for each other, after obviously being together for so long, made Dean's heart ache. Maybe he'll find a love like that, one day. 

The main reason why Dean ever wanted to open an old-fashioned diner in the first place was for the people that wanted to recall the greatness and the fun of a place like this or to show people who were too young about the magic that could be found in a diner. _It might be a little greasy but it was still magic._ It took him several years of working too hard at a local garage to save enough money to put a payment on a rundown florists. Less than a year later, Dean's Diner was officially open for business. The name. funnily enough, took much longer to come up with than the actual menu for the diner. There were hundreds of other potential names: _Wallflower Diner, The Sticky Hideout, Chevy Eats._ But, luckily, Dean’s brother Sam came up with the simple name before Dean could rip out all of his hair due to stress. 

Dean took a lazy look around the customers and it seemed they were content, absorbed in their own conversations or devouring their plates of hot food. The slowest day ever and Dean had no one who could hold a decent conversation for more than 5 minutes. Dean tried to busy himself by washing and scrubbing coffee mugs and sweeping imaginary dirt from underneath one of the tables. _You can never be too clean._ Usually, Jo, the daughter of a family friend, would be sweeping around empty tables or clearing away plates but today was her day off. 

He craned his neck to look over his head at the hanging blackboard that held the set menu as well as the speciality items for the day. _Cherry pie and Homemade biscuits with sausage gravy._ The menu took little to no time to figure out in the beginning. All the classics are on it; _burger with fries, milkshakes and pies_. All of the staples of great "American cooking" were permanently on offer here although the specialities were rotated depending on how the food orders were that week and, more importantly, what Benny wanted to cook.  

Benny was one of Dean's best friends, having worked with each other in the garage and they agreed to dive straight into this venture together. Ben originally was from deep within Louisiana and he was the nicest guy that you could ever wish to meet. His southern drawl brought a warmth to every conversation and people seemed to like him instantly. Although he could seem a little intimidating at times, Benny was a true teddy bear underneath the rough exterior. 

Dean's ears perked up when he heard the opening bars of "Carry on my Wayward Son" from the radio that Benny had playing 24/7 in the kitchen. He chuckles and hums along with the tune as he wipes a few crumbs off the counter before his attention was caught by one of the police officers waving at him. _Back to work._ He picked up a small writing pad and a pen from under the counter. The officers were still talking in a hushed whisper when Dean stood next to their table but, soon, their conversation ceased as they turned their attention to him. 

"How can I help?"

“We’re wondering if you do takeout orders. Me and my partner love your Beignets and wanna take some back to the station with us.”

The male officer appeared to be slightly older than his partner and had a serious, no-BS kind of stare that made Dean stand with his back a little straighter. He had read their name badges as “Hendrikson” and “Mills.” Officer Mills was more easy going and tended to act almost motherly towards Dean whenever her and her partner sat up at the counter. _Although he had seen her lose her temper too._ Hendrikson didn’t seem to like Dean all that much but he certainly loves Benny’s Beignet more than anything else on the menu. Every time that they come into the diner, apart from coffee, it is the only thing that Hendrikson orders.

“We could box up a couple for you guys. Just give me a moment to talk to the man behind the grill.”

Dean flashed his award winning smile once again before retreating to the safety of the kitchen. _Fuck man._ He faked an overdramatic shudder as he walked over to find Benny already making a plate of Beignets.

“Hendrikson gives me the fucking creeps”

“Only ‘cause he’s a cop”

“No Ben, it’s that damn stare of his. It freaks me out. Anyway, they want a box instead of a single order." 

Benny sighed as he reached for a white cardboard box they kept on a higher shelf for any special takeaway orders - specifically when Hendrikson drops in.

“A dozen for the ice cop are on their way.”

Dean was just about to continue joking when he heard the bell above the door chime.  _Duty calls._  He patted Benny on the shoulder as he left the man to his pastries. Dean strained another wide smile as he spotted Hendrikson and Mills waiting for their order at the end of the counter.

“They’re on their way, Officers”

As usual, Hendrikson gave a simple nod of the head and Mills smiled warmly back at Dean. _I like Mills better._ He turned back around, searching under the counter for his small notepad and pen to take the new customers order. 

"Hello there, I'm Dean and what can I..."

Dean lifted his head and instantly met ridiculously blue eyes that stared intently back at him. The man's hair was messy but strangely styled at the same time, random strands proudly sticking out in a variety of directions. Dean could feel his mouth want to hang open as his eyes fell down to the man's powerful jawline covered in dark stubble. He blinked several times to tear his mind back to reality but he could already feel a blush creeping up the back of his neck.  _Fuck, he was in trouble._

"Sorry about that, lost my train of thought for a second. Anyway, my name is Dean and I'm your server for the day so what can I get you?"

“A double cheeseburger and the largest stack of fries that you can fit on the plate, please.”

 _Holy shit._ This man must gargle gravel or something to get his voice that rough and low. Dean’s mouth tried to fall open again but he shook his head as, out of the corner of his eye, he could see an inpatient look from Hendrikson. _Right, Box of pastries._ He grinned and wrote down the relatively short order. 

“Right, I’ll be right back for your drink order.”

Dean tried not to sprint back into the safety of the kitchen and found Benny towards the back entrance, folding up more white takeout boxes for our standing orders.  _Orders that our phoned ahead for people who don't have enough time to sit in and eat._

“Alright now Dean. A dozen for Hendrikson and anyone brave enough to take one away from him”

Dean groaned in frustration as he hit his head against the side of the standing bread oven. _Stupid Hendrikson and hot strangers._ Luckily, it wasn't on otherwise he would have burnt his forehead. Benny simply sighed and pushed the large box into Dean's arms, shoved him towards the connecting door back to the diner.

“Go on Dean, we're only halfway through the day. No time for crashing this early.”

Dean flipped Benny the bird over his shoulder as he slid the box in front of Hendrikson with his best smile.

"There you are Officer Hendrikson. A dozen of our best Beignets from our own Southern Comfort"

He could hear Benny chuckling to himself from the kitchen as Dean grinned at his own joke but Hendrikson was too busy admiring Benny's handiwork to take any notice of Dean's joke. The policeman simply looked at his partner and left with another word.

"I guess I'll pay this time! Asshead!"

Officer Mills was so better mannered than Hendrikson. Even on the bad days, she managed to raise a smile and could easily crack a joke with Dean whilst giving her partner a death stare. She counted out the tab they owed and left Dean a generous tip before winking and following after Hendrikson. He chuckled as he reached for a napkin to place in front of the stranger.

“So what will it be to drink?”

“Mmm, I love the sound of a Banana and Peanut butter milkshake”

 

"Sure thing, Sir." 

 _Right, don't fuck this up._ One of the great things about having such a large counter like this one is that everything needed for any drinks are stored underneath the table-top itself, thanks to some clever building. Dean busied himself with making the milkshake, scooping Peanut Butter and mashed Bananas into a blender followed by ice cream and he was definitely not thinking about the way that the man was staring at him while he worked on the drink. _Well, more specifically, he was staring at Dean's hands._ He grinned a little too proudly as he slid the now filled glass in front of the customer.

“There you go. Your food will be up and done in a few.”

Dean was wiping down the counter and tidying away some of the unused bowls of sugar when Benny chimed to signal that the customer's order was done. _Benny was always quick about getting orders filled._ He hummed quietly as he immediately smelt the delicious meat and his stomach grumbled loud reminding Dean that he had, once again, forgotten to eat breakfast to open an hour or so early for Benny to start on a new pie flavour. _It didn't end well._ He smiled as he placed the large plate of food in front of the customer and the man's face instantly lit up with excitement. 

"Enjoy your meal and call if you need anything."

"Thank you Dean"

The man didn't even look away from his plate of food to speak to Dean but instead grabbed his burger and took the bite that should belong to a starving man and he groaned from deep within his chest at the taste of the gooey cheese against the smoke-flavoured burger. Dean nearly lost it as the man took another large bite and made a noise that should be classed as pornographic. He started to wonder what other interesting noises the man could make if given the right... stimulus. _No, he needed to stay professional here._ Dean busied himself before his mind got any further into that dangerous territory.He spent, at least, five minutes listening to the elderly couple compliment him on the Gumbo before leaving and Dean quickly cleaned up the mess of plates that the group of teenagers left. _He didn't hear the bell above the door as the kids left._

When Dean returned behind the counter, the man had eaten the majority of his burger and started to slowly work his way through his stack of fries. He was, now, the only customer in the whole place so Dean decided that it wouldn't hurt if he took his lunch break, even if it is an hour later than usual. He slipped back into the kitchen to grab a bowl and ladle some of the Gumbo that they kept on the back burner all day before dragging a stool out to the counter, rather close to the man. _Just for a conversation, no other reason._ Dean got through two mouthfuls of the stew before making his own nearly pornographic noise with his eyes rolling slightly. He glanced up to see the stranger staring straight at him, fries still held half-way to his mouth. Dean shrugged his shoulders and smiled shyly.

"The Gumbo here is really good if I do say so myself. We're mainly known for our burgers but people love our Gumbo. I think Benny puts something into it because you seriously can't just have one bowl of it. Do you know what I mean?"

The man nodded and smiled around his mouthful of fries before taking a large sip of his milkshake then clearing his throat to ensure that he was speaking clearly.

"I was recommended your place by my brother. He swore that you had to best burgers in the state and I think he's right."

Dean smiled the best that he could around his own mouthful of prawns and some peppers, not wanting to seem rude if he spoke with his mouth full.

“Thanks Man, I love hearing that our customers actually like our food instead of just putting a brave face on it to be polite to us.”

There was a slight chuckle to his voice but Dean noticed that he man didn't seem to find the joke. The customer simply tilted his head to side slightly as he stared at Dean for a moment before returning his attention to his plate of fries.

“I have tried a cheeseburger in every state and yours is by far the best one I have had.”

“Every state? Really?”

Dean was more than a little sceptical and raised an inquisitive eyebrow, silently enjoying the small smile that was tugging at the corners of the man's lips.  

“Yes. I had a year out of college to experience the world and my older brother convinced me to go on a road-trip with him. At the time, it seemed like a bad idea so I agreed that I would go on one condition that he buys me a burger and shake in every state that we end up in. Anyway, a year later, I was back at college and weighed 20 pounds heavier but it was worth it. He still tells me about places and I try to go to them to see if he's telling the truth." 

Dean chuckled as he thought about his own road-trips with Sam and for the next hour or so, they kept their quite conversation going as they both spoke about the antics that occurred with their brothers. He learnt that the man -  _still lacking a name -_ had several older brothers and he found out that the road-trip brother was famous for pulling pranks. They swapped stories about the variety of pranks that had been pulled on them and the ones that they pulled on their siblings in revenge. Dean made the man really laugh with the tale of putting Nair in Sam's shampoo bottle. 

Sadly, Dean had to take a break from talking to the man as the after school hockey team stopped by and it was all hands on deck for nearly two hours. Every once in a while, whilst Dean was serving the kids sat at the counter, he would remake Mr Blue eyes milkshake before winking at him and sauntering off to refill endless glasses of lemonade. _He hated hockey days._ There was always a thick layer of mud on the floor afterwards and the high-pitched squeals from the kids made him grind his teeth but Dean's wallet couldn't argue at all. Finally, all of the kids left with full stomachs and their parents followed behind them with empty wallets. Dean swept away most of the mud and wiped down the tables in the booth and the counter before returning back to his stool with a tired huff.

Their conversation started again as the man questioned about the recipe for their Gumbo and Dean explained why Cherry was better than Apple as a pie filling. _Apple Pie is only good if served with a wedge of cheese._ Dean only realised that it had grown late when Benny from the kitchen with his coat and flat cap on.  _Damn it._

"Crap. Sorry man but we gotta close up now"

The man looked slightly disappointed but Dean offered him a warm smile in return. 

"Oh, never mind. Thank you very much for the burger and the company, Dean." 

“It’s okay, it was great to talk to someone who understands the greatness of Cherry Pie.”

The man chuckled low and, _oh_ , that was a sweet sound to Dean’s ears. He reached into the back pocket of his black dress trousers and handed Dean his personal card along with a more than generous tip for the meal.

“I hope to see you again soon Dean. Maybe I will try the Gumbo next time”

Dean grinned as wide as he could – _some would say like a Cheshire Cat_ – but it was a sincere smile. He checked the card for a name that he could finally use for the man. Castiel. Castiel Novak.

“Thanks Castiel. There's always a bowl of Gumbo waiting here for you.”

The man. _No._ Castiel smiled back at him as he swung his legs around the stool and left the diner, pausing to offer him and Benny a small wave through the window. Dean sat back down on his own stool. He could feel his head was swimming on an unknown high. _Cute guys always got him weirdly flustered._ It didn’t take long for him and Benny to lock up the Diner and soon Dean headed for the small apartment behind the diner that he called his own. _It wasn't much but it was home for now._ He was so tired, exhausted from the hectic but boring day, that he landed face first into his bed with a small grunt. 

That night, Dean fell asleep to the sound of a rich laugh and too-blue eyes. 


	2. Early Morning Start

 

Dean will never understand why he agreed to open the diner this early. It was barely 5 am. Benny had rudely awakened him from an intriguing dream that involved a certain blue-eyed customer and a can of whipped cream.  _More than a little intriguing._ Being woken early was the first of many things that decided to go wrong this morning; the boiler to Dean's apartment had shut down - for the third time this week - his normal pot of crappy coffee had spilt which ended up burning his right hand and the morning shipment of fresh fruit had failed to turn up.  _Again._  That meant that no pies could be made today. All of this had happened before Dean even had the chance to change out of his pajamas.

Benny still tried to argue that they needed to be awake this early to give the pies amble time to cool before serving any of them.  _Dean always called bullshit on that._ When they were still working at the garage, Dean could easily take a sneaky catnap when trying to either sleep off a hangover or simply because he didn't get enough hours the night before. But, now that he was  _technically_ the owner of his own business, Dean had to be awake and alert at stupidly early hours to ensure that everything was shipshape before opening for the day.  _The only day that Dean could have a lie-in was Sunday when they opened at 8:30am instead of 7am._

The only thing that was currently keeping Dean from falling asleep on the counter was the hope that the hot guy – Castiel – would come back today.  _Maybe he'll order another burger and make those noises again._ Dean knew that he had to stop fantasizing about one of his customers before he started drooling but who could blame him? The man had a serious case of bedhead and his voice -  _fuck, his voice -_ rumbled low in his chest when he talked. Plus, the only action that Dean has seen in the past 6 months was his own right hand and it had been over a year since his last date; a small fact that he wasn't particularly proud of either. It was with a slightly older guy called Alistair, he was a friend of a friend of a friend or something like that. But Dean bailed as soon as he could when Alistair began to suggest going back to his place to have some fun with his girlfriend.  _Dean might be Bi but he doesn't enjoy threesomes like everyone presumes._ His sexuality wasn't a largely held secret in town - most people didn't care - although if you asked anyone in town, they would call him a modern-day Casanova.  _Utter lies._ It was true that when he was younger, his reputation could be said as rightly earned. But, after a certain relationship ended with Dean’s heart being torn to shreds then sleeping on Benny’s sofa for three months with a scratchy pillow under his head and a bottle of bourbon permanently in his hand; he gave up looking for love altogether.  _Love belonged in Emily Bronte novels._

"Wake up, Brother! We got customers."

Dean snorted awake from his own inner monologue slightly as he spotted the two regular older couple walking across the parking lot. If he remembered correctly their names were Bobby and Ellen. They had been together for as long as anyone in town could care to remember although Dean heard from a reliable source – most likely Benny – they were both married before even meeting each other. Ellen owned a small dive bar a few blocks away called The Roadhouse that Dean has been  _slightly_ drunk in too many times to count. There was a weirdly homely atmosphere to the place and he got a discount on the Top Shelf Whiskey if he brought Ellen a slice of pie.  _Business perks._ Bobby, however, scared the living crap out of him. He owned a junk yard across the other side of town but there was rumours that he had been a hit-man 'back in the day.' Different people shared different stories whenever the subject was brought up. Normally after a few drinks or a nosy patron at the Roadhouse would ask Ellen but she would feign innocence and busy herself with cleaning a glass or something.  _Oh, she definitely knew but Dean was smart enough not to ask himself._  They were, now, both sat in their usual seats at the end of the counter; not needing to look at the menu as they have their orders memorized to the exact letter.

Ellen beamed widely at Dean as he made his way over to them with clean cups and fresh coffee. The only unspoken rule of the diner that they agreed on was that the first customers of the day get free coffee – especially if they're crazy enough to arrive this early in the morning. It was nearly always Bobby and Ellen although Sheriff Mills has been known to stop for a cup before heading into work or whilst she was heading home from a night shift. 

“Hey there Honey, how are you this morning?”

A tired smile tugged at the corners of Dean's mouth at the motherly warmth in Ellen's voice but, sadly from experience, he knew that she could cut you down with her words if you were acting like a fool.  _Throwing darts with a blindfold, dancing on top of the pool table, singing badly at karaoke..._ The list goes on and on. 

“As fine as the day is long, Miss Ellen.”

Dean always noticed that his slight Southern twang became more pronounced whenever he spoke to Ellen.  _Maybe it was a respect thing._ He carefully set the full mugs of coffee in front of both of them with an easy grin before hurriedly disappearing into the kitchen to fetch their usual. Dean could feel the weight of Bobby's glare on the back of his neck and he was slightly thankful to be out of his sight for a few moments.  _It was still too early to deal with customers._

“Benny! Two cheese omelettes, hash-browns and a basket of fries to share.”

No response.

“Come on man! Don’t want to keep Miss Ellen waiting for her breakfast."

Still nothing.  _Huh._ It wasn’t like Benny to just abandon the kitchen without shouting through to Dean. He glanced into the cloak room in the left back corner of the kitchen. Benny, occasionally, sneaked in there for a short cigarette break between orders.  _But no sign of him._  Dean checked the bathroom, the pantry and the deep freezer.

Still nothing.

"Brother, come on. We ain't 5 and I'm not playing hide and seek when we have customers."

The back door was slightly ajar -  _weird._ Dean was absolutely sure he closed it properly after bringing up the day's bread delivery otherwise a couple of stray cats would get into the kitchen in search of food. He stuck his head out the door, scanning the darkened are for Benny but no sign of him. The only time that Benny ever left his post like this was the occasion that he had food poisoning but Dean easily found him in the bathroom before sending him home for the rest of the day.  _Sammy had been visiting so he took orders while Dean manned the grill._ He jolted with a start when a firm hand was planted on his shoulder and he spun on the spot to be greeted with Benny's wide grin. 

“Not fucking funny Benny!”

“Of course it was.”

Benny crossed his arms over his chest with a deep chuckle but Dean rolled his eyes, closing the back door slightly more forcefully than he intended to. 

"Where the hell did you go, anyway?”

_Nice subject change, Winchester._

"That guy you were drooling over the other day came to the side door asking for you."

Dean felt his heart leap sideways in his chest and the butterflies in his stomach start fluttering.  _Stop it._  This was ridiculous; his body was reacting like this at the simple mention of Castiel. He definitely wasn’t a 14-year-old girl and this wasn’t some sickly rom com that ended in Dean and Castiel running towards each other before sharing a long kiss in the rain. 

"What did he want?"

He had to stop his voice from shaking with anticipation but Dean did glare slightly as the smile on Benny's face grew wider.  _Mind reader._ Benny had an unusually good sense whether Dean truly liked someone or not and, by his smug grin, Ben knew that Dean had it bad for Castiel already. 

“He wanted to give you his phone number but the sign hadn’t been flipped to ‘open’ yet so when he spotted me in the alley having a smoke, he gave it to me to deliver to you.”

Benny handed him a carefully folded piece of paper with his name neatly printed on the top before walking into the small office for a moment to answer the phone. _Calm down, Winchester._ Dean was trying to ease the hard thrumming of his heart on the inside of his chest whilst unfolded the page, his eyes flicking over the neatly written words.

“ ** _Dean,_**

**_Unfortunately, I forgot to give you my phone number the last time that I saw you and I'm unsure when I will be available to stop at the diner again. Perhaps we could grab a drink together._ **

**_Hopefully, I will see you soon._**  
**_Cas._**

**_Ps. Apologies my future absences but the life of a teacher can be busy."_ **

 

Underneath the short message were 10 digits in a straight line, boldly printed for easier reading and Dean suddenly felt his hands becoming sweaty. _Oh god, he was acting like a teenage girl._ It was just a phone number but, it was from a seriously good-looking teacher and he was more than a little rusty about the whole "dating another human" thing. 

“You okay there, Dean? Not gonna faint or anything, are you?”

Benny's deep voice brought Dean back to reality and, although he knew that Ben was joking, he could feel his knees weaken underneath him. Fuck, this was ridiculous. It was just a simple phone number, nothing important. In the past, Dean collected numbers from girls like it was nothing but, one number from a guy and he was already swooning and blushing like a naive schoolgirl.  

“No man. I'm fine. Normal breakfast plates for Miss Ellen and Bobby.”

“Sure thing, Brother. Why don’t you give your man a call?”

Benny was chuckling as he sauntered over to the hot grill, leaving Dean to stand on his own by the back door for a minute. Was he actually going to call Castiel? The guy had only just given in his phone number and he could be busy or something. The more time that Dean stood there; the more that he tried to convince himself that it was a bad idea to call Castiel so soon but he couldn't stop the excited buzz of anticipation underneath his skin. _Fuck it._ He slipped into the small office for some privacy, shutting the door behind himself to ensure that Benny couldn't eavesdrop. Dean could feel his heart pounding in his chest. Dean scrubbed a hand over his face, tiredly grumbling into his palm as he stared down at the creased piece of paper on his desk. His stomach kept flipping, causing another wave of uneasy nausea raising up into his throat. _He could do this._ He was Dean fucking Winchester! He didn't get flustered or blush at the simple though of some hot guy. He could reduce anyone into a babbling mess with a simple smile and a wink of his eye. Before Dean could talk himself out of it again, he quickly dialled the number into the office phone. The ringing tone only added to the butterflies in his stomach, the acidic feeling rising up again.

"Hello?"

A deep voice rumbled through the line and Dean let out a shaky breath that he didn't know that he was holding, his fingers curled tightly around the receiver.  _Speak Winchester. Use your words and speak before he hangs up._

"H-Hey Castiel? This is Dean Winchester - from the diner."

Dean grimaced as he heard his own voice crack into the speaker park of the phone in his hand. _Try to play it cool._ He had to get a control on the nerves that were running rampant in his stomach otherwise Castiel was going to think that he is a weirdo and never agree to actually going out on a date with him.  _Make jokes, flirt, be Dean Fucking Winchester._ His own inner monologue was almost distracting him too much from the conversation that Castiel was attempting to hold with him.

"Ah, you got my note from Mr Lafitte."

Dean had to hold back a bark of laughter at the use of Benny's surname and the formal tone to Castiel's voice; chuckling low whilst a somewhat shaky hand combed through the longer strands of his own hair. 

"I'm sorry man, it's just still a little weird for anyone to say his last name. You can call him Benny, he only answers to Lafitte if he's in trouble or trying to make an impression... or both."

That earned a small rumble of laughter from Castiel and Dean could feel a small warm bubble of affection beginning to burn in the center of his chest. _This was getting out of hand._ He had only met Castiel once and he was already acting like a lovesick idiot. For all that he knew; this Castiel could be a serial killer that kept photographs of each of his victims and he was next on the list. _Ted Bundy was always noted to be charming and charismatic._ There was a small tap at the door and Dean lifted his eyes to see Benny was mouthing something about college students. Dean waved a dismissive hand at him, accidentally sighing into the phone.

“Damn it. I may have to cut our call a little short. Sorry but students have just turned up for their morning fix of caffeine.”

Another soft sound of laughter that sent Dean's heart leaping wildly in his chest.  _This was stupid._

“Ah, I know how they must feel returning to college after such a long break.”

 _That's right._ Mr Blue-eyes was a teacher and that fact brought up some questionable images to Dean's mind that was definitely securing him a one-way ticket to hell.

"Well, we start serving coffee at 7am on the dot so you could always pick up a cup before heading into work for the day." 

There was something hopeful behind his voice and Dean was smiling to himself at the prospect of seeing Castiel most mornings with his absurdly messy bed-head. The rest of Castiel's words were drowned out by a louder knock at the door from Benny, gesturing more energetically than before. Dean held up a finger to ask for one more minute on the phone and he easily spotted the roll from Benny's eyes before the chef walked into a different part of the kitchen. 

“Crap. Anyway, about that drink that you mentioned in your note. The only nights that I have off this week are Saturday and Sunday but I could make arrangements any night that you’re available.”

 _Wow; that definitely sounded less needy in his mind._  Dean mentally slapped himself on the back of the head, resting his forehead on the edge of the desk to keep the threatening headache that was building behind his eyes at bay. 

“I have some prep work to set up for my students for their first week back but I'm more than sure that I am free for a drink this Saturday. I could meet you outside the diner at 8 and we could take it from there?”

“That sounds like a plan to me Cas. Um, I'll text you when I'm finished up here?”

“Of course, Dean.”

“Have fun with your students and don’t work too hard now. See you then.”

After an equally short and awkward goodbye; Dean hung up the phone with a smile plastered across his face. His heart was still trying to do complete somersaults inside of his chest. _God, he couldn’t act like a normal person for once in his life, could he?_ He shook his head to try to rid his own head of the dark thoughts that raised themselves from the back of his mind.  _Not now._ Dean returned to the front of the diner, frantically taking a multitude of orders and pouring coffee into mugs for the desperate teens. 

_Maybe today wasn't going to be such a crap-shoot after all._

**Notes for the Chapter:**

> My sincerest apologies that this chapter took so long to edit and update - Life is busy and I suck at multitasking. Anyway, keep an eye out for more updates. 
> 
> Thanks for reading.   
> If you have any comments, please leave them down below.   
> Love ya x


	3. Heated Meeting

**Summary for the Chapter:**

> There is Transphobia in this chapter - Just a warning.   
> If you don't feel comfortable with reading that, don't do it.   
> Much love.

Castiel hated teacher meetings. There was no sugar coating it or pretending that he could happily sit through them as if they weren't torturous when he could be at home or out on a date with a green-eyed hunk. _Saturday needed to hurry up._ Thankfully, he wasn't the only one that absolutely loathed being still here this late when all the staff could be somewhere more important. Cas glanced down to his watch for the hundredth time, praying for a swift end to this weekly powwow. 

 _6:39pm._  It had only been three agonizing minutes since the last time that he checked his watch and Castiel was ready to let his head fall down onto the desk, out of pure boredom. The meetings would make more sense to him if they were held on Monday or, even, Friday but it was decided to hold them on Wednesday and that decision was our of Castiel's control by a large margin.  _Maybe the board of directors were really robots in Monkey suits._

“Do you have somewhere else to be Mr Novak?” 

The voice startled Castiel from his boredom and his back straightened instantly, his hands folding neatly together in his lap. An old habit that he still, unfortunately, held from his childhood when his mother would force him to attend church with her. Cas looked down the long table to Raphael, the principal, who was sat at the head of it and to Uriel, the vice-principal who was obediently seated next to her.

Raphael was a tall, slender woman with dark skin; always smartly dressed in a simple grey suit that was tailored to her thin frame and cinched at the waist to add more femininity to the garment. Uriel was a more robust man, his jaw set firm with every emotion and he had a nasty habit of looking down at the other teachers with snide remarks about their teaching methods or their physical appearances. Both of them were staring intently straight at Castiel. He didn't need to look around the table to know that everyone was looking at him. _Crap._ The weight of the gazes from the other staff was unnerving and Castiel could feel himself shrink back in his seat, head lowering an inch in submission. 

“No, I don’t this evening. My apologies, Raphael.”

There was a short pause before Raphael began to speak again, her voice fading into the background and he sighed under his breath in defeat about truly being stuck here with the other staff. It had been nearly two years since Castiel made the decision to transfer to Kansas from a private school in Chicago. In that time, he hadn’t become close to any of the other teachers; except for Charlie Bradbury and Gabriel Morton. 

Charlie was the head of the IT department that had more than a profound love for Star Trek and Katrine & The Waves. She was shorter than Castiel – by more than a couple of inches – but her lively personality definitely made up for her lack of height and it was more than easy to point Charlie out in a crowd. Her hair was a bright shade of orange, which was cut into a wavy little bob and she bypassed the suggested dress requirements for the staff to wear different slogan t-shirts and jeans. They had become friends after Charlie had bear hugged Castiel on his very first day when he accidentally walked into the middle of her supervising a class, looking for his own classroom. _He wasn't even in the right building._ Since then, Charlie had dragged Cas to every LARPing event, outside of school, and every double date with her girlfriend, Gilda. Charlie had, thankfully, stopped inviting Cas to double dates after an incident when an old friend dumped an entire plate of pasta into his lap and then proceeded to storm out of the restaurant. It took most of Castiel's self-control to restrain himself from bursting into a fit of laughter until he was safely in the back of a taxi on his way home that evening. 

Gabriel was one of two home economics teacher who shared the same mentality of an 8-year-old and had a slight concerning addiction to anything that contained sugar. _Ironic for someone who was meant to show students how easy healthy cooking could be._ He was almost the same height as Castiel, golden hair barely touching his shoulders and a wicked sense of humor that riled Uriel on too many occasions. Gabriel had a rebellious tendency to bend the rules to his own liking. Sometimes, he would order pizza from a local takeaway in the middle of a long school day and share it with his older students or he would throw water balloons at the teachers running around the track field on sports day. There was one incident during Castiel’s first week which ended with Gabriel getting suspended for a whole month and a senior student becoming high by a batch “special” brownies. They never talked about that when Gabriel returned to work although he did abide by the school rules for a week as he was on probation before he returned to his disobedient ways. 

"I don't get why they have to wear them."

Castiel tuned back into the conversation as he recognized the irritated edge to Charlie's voice, a small crease appearing between his brows from confusion. She was seated directly opposite him, donning her favorite 'The Empire Strikes Back' tee - which had faded to beyond recognition at this point in time. Cas glanced around to the other staff established around the table; not a single one seemed to be reacting in the same way as Charlie. Most of them had their heads bowed slightly or their attention was on an imaginary patch of dirt on the floor, radiating an uncomfortable atmosphere in the room. _What was going on?_

"Because we need to know what our students are, Miss Bradbury. That is why we are enforcing the wristbands."

Wristbands? Castiel held back an annoyed huffed as he leaned forward in his chair, his elbows now resting on the table in front of him and his eyes bounced between the stone expression of Raphael and the annoyed look of Charlie. _Something was wrong._ Charlie was nearly never bothered by anything. He would give everything to be at home with a cup of Earl Grey, staring at finished lesson plans for the start of next week. However, thanks to the sadistic devising of Uriel, he would not be able to finish everything tonight.

“We don’t need to know the sexuality or gender identity of our students!”

Castiel snapped his full attention to his friend, mouth ajar by an inch at the abrupt exclaim from Charlie. He had hardly heard her raise her voice like that before - the only other time was after catching several students writing hateful and discriminating language on another student’s book behind their back. She was ticked off for the rest of the week and not even Gilda could get her to smile. _Raphael was hesitant to suspend the students until Charlie threatened to call the board of directors._ Castiel could clearing see the angered heat rising in Charlie's cheeks as she stared down at a teacher a few seats to the left of Cas instead of Raphael or Uriel. The teacher in question was Anna Collins; a mre than strict Geography teacher who seemed to not like Charlie or Cas, enforcing the "Don't ask, Don't tell" policy at school although there were several LGBT+ members of staff. _Charlie, Cas, Garth - one of the technology teachers._ The shift from Charlie's normally chipper disposition seemed to shake everyone in the room; even Uriel grew still in his place next to Raphael.

“It is to ensure the safety of our other students and ensure that they are using the correct bathroom.”

The correct bathroom was the one that aligned with the gender that the person wanted to be identified as. _No ifs or buts._ Cas could see a matching blush rising in Anna’s cheeks, a true indicator of an impending outburst of anger from the female teacher. Cas had been quite fortunate, so far, that he had never been on the receiving end of a verbal lashing from Anna. Sadly, he had been a witness to the dismantle of the students from her stern voice as well as sharp tongue and a glare that could rival Uriel's that had obviously been perfected over several years from teaching. 

"That is absolute bullsh..." 

"Enough!" 

Everyone around the table – _apart from Charlie_ – flinched at the barked order from Uriel; the man standing from his seat to tower over the other teachers and, out of the corner of his eye - Castiel saw Charlie's top lip twitch from being cut off mid-sentence. If he was being honest, Charlie was right and it was absolutely BS but Castiel wasn't confident enough to face down the more mature members of staff. 

“Ms Collins, if you wish to further this issue than I suggest that you form a more solid argument that will be presented again at the staff meeting towards the end of the month. Miss Bradbury…”

Castiel took a single glance at Charlie and knew that she wasn't listening anymore, her foot scuffing at the carpet underneath the table in annoyance and the Vice-Principal decided to not speak any further before sitting back in his chair.  _Thank God that Uriel stopped the disagreement before Charlie threw a chair at Anna._ Castiel leaned back in his chair again and offered a small smile to his friend when she lifted her head to look over at him but she didn't return it. The rest of the teachers were, again, paying attention to Raphael as she reads through several complaints that weren't dealt with at the last staff meeting and Castiel stole a glance to his watch again. 

_7:06pm._

It was going to be another long night. 

**Notes for the Chapter:**

> Thank you so much for reading.   
> If you have any comments, please leave them down below and I am trying my best to update as much as possible but I suck at getting past writer's block. 
> 
> Love you x


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